Diethyl Ether → HCID 67520924, compound

HRID 1925929Notes

Reaction equation

HRID 1925929 reaction equation
C[O:2][C:3](=[O:25])[C@@H:4]([N:11]1[CH2:15][C:14]2=[CH:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=3[O:23][CH:13]2[C:12]1=[O:24])[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Li+].CCOCC>C1COCC1.O>[CH:6]1([CH2:5][C@H:4]([N:11]2[CH2:15][C:14]3[CH2:16][C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=4[O:23][C:13]=3[C:12]2=[O:24])[C:3]([OH:25])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 3939Lithium HydroxideHCID 67521094HCID 67521094, compound

Product 1

HCID 67520924HCID 67520924, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a magnetically stirred mixture of (S)-3-Cyclopentyl-2-(3-oxo-3,3a-dihydro-1H-chromeno[2,3-c]pyrrol-2-yl)-propionic acid methyl ester (0.64 g, 1.88 mmol) in THF (9 mL) and water (3 mL) was added lithium hydroxide (0.102 g, 2.44 mmol). After addition was complete the mixture was stirred at 25° C. for 2 hours. The reaction mixture was poured into water and ether and the layers separated. The aqueous layer was made acidic with 2N HCl and extracted with three portions of ethyl acetate. The combined ethyl acetate fractions were washed with a saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to afford (S)-3-Cyclopentyl-2-(3-oxo-3,9-dihydro-1H-chromeno[2,3-c]pyrrol-2-yl)-propionic acid as a white solid, 500 mg (81% yield). ESI-LRMS m/e calcd for C19H21NO4 [M+] 327, found 328 [M+H+]. (Note: The double bond isomerizes during the course of the reaction based on NMR spectrum)

Workup

  1. additionAfter addition
  2. customthe layers separated
  3. extractionextracted with three portions of ethyl acetate
  4. washThe combined ethyl acetate fractions were washed with a saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6e1120fd35d944959aca931f3cb342ea
Source dataset
uspto-grants-2012_05
Patent number
US08178689B2

Reaction notes

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